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Terpinolene
- Family: Plantae - Juglandaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | CC1=CCC(=C(C)C)CC1 |
|---|---|
| InChI | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3 |
| InChIKey | MOYAFQVGZZPNRA-UHFFFAOYSA-N |
| Formula | C10H16 |
| HBA | 0 |
| HBD | 0 |
| MW | 136.24 |
| Rotatable Bonds | 0 |
| TPSA | 0.0 |
| LogP | 3.45 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 10 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 136.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cupressus dupreziana | Cupressaceae | Plantae | 329083 |
| 2 | Cupressus sempervirens | Cupressaceae | Plantae | 13469 |
| 3 | Cupressus arizonica | Cupressaceae | Plantae | 49011 |
| 4 | Conyza bonariensis | Asteraceae | Plantae | 91242 |
| 5 | Commiphora quadricincta | Burseraceae | Plantae | 2248429 |
| 6 | Plectranthus marrubioides | Lamiaceae | Plantae | 204214 |
| 7 | Juglans regia L | Juglandaceae | Plantae | 16718 |
Showing of synonyms
Terpinolene
586-62-9
Isoterpinene
Terpinolen
Alpha-Terpinolene
4-Isopropylidene-1-methylcyclohexene
P-Mentha-1,4(8)-diene
1,4(8)-p-Menthadiene
Nofmer TP
Tereben
P-Menth-1,4(8)-diene
1,4(8)-Terpadiene
1-Methyl-4-(1-methylethylidene)cyclohexene
1-Methyl-4-isopropylidene-1-cyclohexene
FEMA No. 3046
FEMA Number 3046
1-Methyl-4-(1-methylethylidene)-1-cyclohexene
HSDB 5702
EINECS 209-578-0
UNII-N9830X5KSL
CHEBI:9457
N9830X5KSL
DTXSID0027222
1-methyl-4-(propan-2-ylidene)cyclohexene
AI3-24378
DTXCID507222
EC 209-578-0
D-1-methyl-4-isopropenyl-1-cyclohexene
4-ISOPROPYLIDENE-1-METHYLCYCLOHEXANE
CYCLOHEXENE, 1-METHYL-4-(1-METHYLETHYLIDENE)-, (R)-
209-578-0
1-methyl-4-(1-methylethylidene)cyclohexane
Cyclohexene, 1-methyl-4-(1-methylethylidene)-
1-methyl-4-propan-2-ylidenecyclohexene
P-Meth-1-en-8-yl-formate
4-isopropylidene-1-methyl-cyclohexene
.gamma.-Terpinolene
Terpinolene (>85%)
1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
MFCD00049191
1-methyl-4-(1-methylethylidene)-cyclohexene
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9CI)
1-methyl-4-(propan-2-ylidene)cyclohexene p-mentha-1,4(8)-diene
UN2541
Delta-Terpinene
Alpha -Terpinolene
Terpinolene Natural
.alpha.-Terpinolene
Terpinolene 95 PF
.alpha.- Terpinolen
Terpinolene, >=90%
TERPINOLENE with GC
TERPINOLENE [FHFI]
TERPINOLENE [HSDB]
Bmse000504
CHEMBL454697
Terpinolene, analytical standard
FEMA 3046
AAA58662
Tox21_303268
AKOS028108377
FS-6812
LMPR0102090062
MSK014184-100M
Terpinolene, technical, >=85% (GC)
UN 2541
Terpinolene, purum, >=95.0% (GC)
NCGC00256963-01
CAS-586-62-9
DB-053242
Terpinolene 1000 microg/mL in Isopropanol
NS00005520
T0817
Terpinolene [UN2541] [Flammable liquid]
Terpinolene Solution in Methanol, 100ug/mL
C06075
EN300-125038
Alpha-Terpinolene 1000 microg/mL in Isopropanol
1-Methyl-4-(1-methylethylidene)-1-cyclohexene #
1-Methyl-4-(1-methylethylidene)cyclohexene, 9CI
Q2405051
Z1255360533
9LR
- Cheraif I, Jannet HB, et al. (2007). Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene. Biochemical Systematics and Ecology,2007,35,813 -820. [View]
- Mabrouk S, Elaissi A, et al. (2011). Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia. Natural Product Research,2011,5(1),77-84. [View] [PubMed]
- Boukhari F, Tigrine-Kordjani N, et al. (2013). Phytochemical Investigation by Microwave-Assisted Extraction of Essential Oil of the Leaves of Walnut Cultivated in Algeria. Helvetica, 2013, 96(6), 1168-1175. [View]
- Omolo MO, Okinyo D, et al. (2004). Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry,2004,65(20),2797-2802. [View] [PubMed]
- Assad YOH, Torto B, et al. (1997). Seasonal variation in the essential oil composition of Commiphora quadricincta and its effect on the maturation of immature adults of the desert locust, Schistocerca gregaria. Phytochemistry,1997,44(5),833-841. [View] [PubMed]
- Pauly G, Yani A, et al. (1983). Volatile constituents of the leaves of Cupressus duprezzana and Cupressus semper virens. Phytochemistry,1983,22(4),957-959. [View]
Pubchem:
11463
Cas:
586-62-9
Zinc:
ZINC000000968225
Kegg Ligand:
C06075
Chebi:
9457
Nmrshiftdb2:
20230529
Metabolights:
MTBLC9457
Chembl:
CHEMBL454697
Comptox:
DTXSID0027222
Pdb Ligand:
9LR
CPRiL:
119236
SMILES: C=C1CC=CCC1
Level: 0
Mol. Weight: 136.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.69
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.5
- Plasma Protein Binding
- 5.59
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.15
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.17
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.08
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.46
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 2.79
- Rat (Acute)
- 1.61
- Rat (Chronic Oral)
- 1.77
- Fathead Minnow
- 4.15
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 184.44
- Hydration Free Energy
- -0.12
- Log(D) at pH=7.4
- 2.29
- Log(P)
- 4.61
- Log S
- -4.07
- Log(Vapor Pressure)
- -0.18
- Melting Point
- -38.02
- pKa Acid
- 12.16
- pKa Basic
- 8.9
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8494 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8494 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8232 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8232 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.8173 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.8173 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.8071 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.8071 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7858 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7858 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7846 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7846 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7773 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7773 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7747 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7747 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7733 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7733 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7679 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7679 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7670 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7670 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7670 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7670 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7658 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7658 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7655 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7655 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7638 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7638 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7616 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7616 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7553 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 2 | 0.7553 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7551 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7551 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7543 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7543 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7533 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7533 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7516 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7516 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7461 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7461 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7449 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7449 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7442 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7442 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7428 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7428 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7388 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7388 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7371 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7371 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7355 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7355 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7319 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7319 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7310 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7310 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7286 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7286 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7266 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7266 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7266 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7266 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7261 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7261 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7234 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7234 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7217 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7217 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7141 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7141 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7131 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7131 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7073 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7073 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7069 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7069 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7021 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7021 |